Inhibition of human muscle-specific enolase by methylglyoxal and irreversible formation of advanced glycation end products

Journal of Enzyme Inhibition and Medicinal Chemistry

Volumn 24, Issue 2, 2009, Pages 356-364

  Pietkiewicz, Jadwiga ^a   Gamian, Andrzej ^a,b   Staniszewska, Magdalena ^b   Danielewicz, Regina ^a  

^a WROCLAW MEDICAL UNIVERSITY   (Poland)

^b INSTITUTE OF IMMUNOLOGY AND EXPERIMENTAL THERAPY   (Poland)

Author keywords

End products; Enolase; Glycation; Inhibition; Methylglyoxal

Indexed keywords

2 PHOSPHO DEXTRO GLYCERATE; ADVANCED GLYCATION END PRODUCT; BUFFER; ENOLASE; GLYCERIC ACID; MAGNESIUM ION; METHYLGLYOXAL; PHOSPHATE; PHOSPHOENOLPYRUVATE; TRYPSIN; UNCLASSIFIED DRUG; ENZYME INHIBITOR;

ALKALINITY; ARTICLE; CONCENTRATION RESPONSE; CULTURE MEDIUM; ENZYME ACTIVITY; ENZYME ASSAY; ENZYME INACTIVATION; ENZYME INHIBITION; ENZYME KINETICS; ENZYME MECHANISM; ENZYME SPECIFICITY; ENZYME SUBSTRATE; HUMAN; PH; PRIORITY JOURNAL; PROTEIN DEGRADATION; SYNTHESIS; DRUG ANTAGONISM; KINETICS; METABOLISM;

ENZYME INHIBITORS; GLYCOSYLATION END PRODUCTS, ADVANCED; HUMANS; HYDROGEN-ION CONCENTRATION; KINETICS; PHOSPHOPYRUVATE HYDRATASE; PYRUVALDEHYDE; SUBSTRATE SPECIFICITY;

EID: 68049098142     PISSN: 14756366     EISSN: 14756374     Source Type: Journal    
DOI: 10.1080/14756360802187679     Document Type: Article

References (50)

1. Wold F. Enolase. In: Boyer PD, editor. The enzymes. 3rd ed. New York: Academic Press; 1971. p 499-538.
2. Lebioda L, Stec B. Mechanism of enolase-Mg2p-2-phosphoglycerate/ phosphoenolpyruvate complex at 2A ° resolution. Biochemistry 1991;30:2817-2822.
3. Nozais M, Merkulova T, Keller A, Janmot Ch, Lompre AM, D'Albis A, Lucas M. Denervation of rabbit gastrocnemius and soleus muscles. Effect on muscle-specific enolase. Eur J Biochem 1999;263:195-201.
4. Ulrich P, Cerami A. Protein glycation, diabetes and aging. Recent Prog Horm Res 2001;56:1-21.
5. Singh R, Barden A, Mori T, Beilin L. Advanced glycation endproducts. Diabetologia 2001;44:129-146.
6. GhoshMoulick R, Bhattacharya J,Roy S, Basak S, Dasgupta AJ. Compensatory secondary structure alterations in protein glycation. Biochim Biophys Acta 2007;1774:233-242.
7. Sims TJ, Rasmussen LM, Oxlund H, Bailey AJ. The role of glycation cross-links in diabetes vascular stiffening. Diabetologia 1996;39:946-951.
8. Turk Z, Ljubic S, Turk N, Benko B. Detection of autoantibodies against glycation endproducts and AGEimmune complexes in serum of patients with diabetes mellitus. Clin Chim Acta 2001;303:105-115.
9. Chibber R, Molinatti PA, Rosatto N, Lambourne B, Kohner EM. Toxic action of advanced glycation end products on cultured retinal capillary pericytes and endothelial cells: Revelance to diabetic retinopathy. Diabetologia 1997;40: 156-164.
10. Suzuki D, Miyata T, Saotome N, Horie K, Inagi R, Yasuda Y, Uschida K, Izuchara Y, Yagame M, Sakai M, Kurokawa K. Immunohistochemical evidence for increased oxidative stress and carbonyl modification of proteins in diabetic glomerular lesions. J Am Soc Nephrol 1999;10:822-832.
11. Duhaiman AS. Glycation of human lens proteins from diabetic and nondiabetic senile cataract patients. Glycoconj J 1995;12: 618-621.
12. Aso Y, Inukai T, Tayama K, Takemura Y. Serum concentrations of advanced glycation end products are associated with development of atherosclerosis as well as diabetic microangiopathy in patients with type 2 diabetes. Acta Diabetol 2000;37: 87-92.
13. Gomes R, Sousa Silva M, Quintas A, Cordeiro C, Freire A, Pereira P, Martins A, Monteiro E, Barroso E, Ponces-Freire A. Argpyrimidine, a methylglyoxal-derived advanced glycation end product in a familial amyloidic polyneuropathy. Biochem J 2005;385:339-345.
14. Loske C, Gerdemann A, Schelp W, Wycislo M, Schnizel R, Palm D, Riederer P, Munch G. Transition metal-mediated glycoxidation accelerates cross-linking of b-amyloid peptide. Eur J Biochem 2000;267:4171-4178.
15. Thornalley PJ. Dicarbonyl intermediates in the Maillard reaction. Ann N Y Acad Sci 2005;1043:111-117.
16. Philips SA, Thornalley PJ. The formation of methylglyoxal from triose phosphates. Investigation using a specific assay for methylglyoxal. Eur J Biochem 1993;212:101-105.
17. Knowles JR. Enzyme catalysis: Not different, just better. Nature 1991;350:121-124.
18. Ahmed N, Battah S, Karachalias N, Babaei-Jadidi R, Horanyi M, Baroti K, Hollan S, Thornalley PJ. Increased formation of methylglyoxal and protein glycation, oxidation and nitrosation in triosephosphate deficiency. Biochim Biophys Acta 2003; 1639:121-132.
19. Beisswenger PJ, Howell SK, Smith K, Szwergold BS. Glyceraldehyde 3-phosphate dehydrogenase activity as an independent modifier of methylglyoxal levels in diabetes. Biochim Biophys Acta 2003;1637:98-105.
20. Thornalley PJ, Langborg A, Minhas H. Formation of glyoxal, methylglyoxal and 3-deoxyglucosone in the glycation of proteins by glucose. Biochem J 1999;344:109-116.
21. Thornalley PJ. Pharmacology of methylglyoxal: Formation, modification of proteins and nucleic acids and enzymatic detoxification-a role in pathogenesis and antiproliferative chemotherapy. Gen Pharmacol 1993;27:565-573.
22. Ray M, Ray S. Aminoacetone oxidase from goat liver. Formation of methylglyoxal from aminoacetone. J Biol Chem 1987;262:5974-5977.
23. Thornalley PJ. Glyoxalase I-structure, function and critical role in the enzymatic defense against glycation. Biochem Soc Trans 2003;31:1343-1348.
24. Szwergold BS, Beisswenger PJ. Enzymatic deglycation-a new paradigm or an phenomenon? Biochem Soc Trans 2003;31: 1428-1432.
25. Takahashi K. The reaction of phenylglyoxal with arginine residues in proteins. J Biol Chem 1968;243:6171-6179.
26. Seidler NW, Kowalewski C. Methylglyoxal-induced glycation affects protein topography. Arch Biochem Biophys 2003;410: 149-154.
27. Kang JH. Modification and inactivation of human Cu,Znsuperoxide dismutase by methylglyoxal. Mol Cells 2003;15: 194-199.
28. Halder J, Ray M, Ray S. Inhibition of glycolysis and mitochondrial respiration of Ehrlich ascites carcinoma cells by methylglyoxal. Int J Cancer 1993;54:443-449.
29. Biswas S,RayM, Misra S, DuttaDP,Ray S. Selective inhibition of mitochondrial respiration and glycolysis in human leukaemic leucocytes by methylglyoxal. Biochem J 1997;323:343-348.
30. Lee HJ, Howell SK, Sanford RJ, Beisswenger PJ. Methylglyoxal can modify GAPDH activity and structure. Ann N Y Acad Sci 2005;1043:135-145.
31. Morgan PE, Dean RT, Davies MJ. Inactivation of cellular enzymes by carbonyl and protein-bound glycation/glycoxidation products. Arch Biochem Biophys 2002;403:259-269.
32. Gomes RA, Miranda HV, Silva MS, Graca G, Coelho AV, Ferreira AE, Cordeiro C, Freire AP. Yeast protein glycation in vivo by methylglyoxal. Molecular modification of glycolytic enzymes and heat shock proteins. FEBS J 2006;273: 5273-5287.
33. Witkowska D, Pietkiewicz J, Szostko B, Danielewicz R, Mas?owski L, Gamian A. Antibodies against human muscle enolase recognize a 45-kDa bacterial cell wall outer membrane enolase-like protein. FEMS Immunol Med Microbiol 2005; 45:53-62.
34. Wold F, Ballou E. Studies on the enzyme enolase. I. Equilibrium studies. J Biol Chem 1957;227:301-312.
35. Baranowski T, Wolna E. Enolase from human muscle. In: Colowick SP, Kaplan NO, editors. Methods in enzymology., Vol.XLII, New York: Academic Press; 1975. p 335-338.
36. Laemmli K. Cleavage of structural proteins during the assembly of the head of bacteriophage T 4. Nature 1977;227: 680-685.
37. Pietkiewicz J, Kustrzeba-Wójcicka I, Wolna E, Wolny M. Purification and properties of enolase from carp (Cyprinus carpio) muscle. Comparison with enolases from mammals muscles and yeast. Comp Biochem Physiol 1983;75B: 693-698.
38. Lineweaver H, Burk D. The determination of enzyme dissociation constants. J Am Chem Soc 1934;56:658-666.
39. LoTW,Westwood ME, Mc Lellan AC, Selwood T, Thornalley PJ. Binding and modification of proteins by methylglyoxal under physiological conditions. J Biol Chem 1994;269: 32299-32305.
40. Martins AM, Cordeiro CA, Ponces Freire AMJ. In situ analysis of methylglyoxal metabolism in Saccharomyces cerevisiae. FEBS Lett 2001;499:41-44.
41. Munch G, Schicktanz D, Behme A, Gerlach M, Riederer P, Palm D, Schinzel R. Amino acid specifity of glycation and protein-AGE crosslinking reactivities determined with SPOT library. Nat Biotechnol 1999;17:1006-1010.
42. Wilker SC, Chellan P, Arnold BM, Nagaraj RH. Chromatographic quantification of argpyrimidine, amethylglyoxal-derived product in tissue proteins: Comparison with pentosidine. Anal Biochem 2001;290:353-358.
43. Pietkiewicz J, Kustrzeba-Wó jcicka I, Wolna E, Wolny M. Chemical modification of histidine, tyrosine, tryptophan and cysteine residues in carp (Cyprinus carpio) muscle enolase. Biochem Inter 1987;14:805-814.
44. Pietkiewicz J, Wolny M. Inactivation of enolase from carp (Cyprinus carpio) muscle by 2,3-butanedione. Biochem Inter 1991;23:69-74.
45. Poyner RR, Cleland WW, Reed GH. Role of metal ions in catalysis by enolase: An ordered kinetic mechanism for a single substrate enzyme. Biochemistry 2001;4:8009-8017.
46. Chai G, Brewer JM, Lovelace LL, Aoki T, Minor V, Lebioda L. Expression, purification and the 1,8A ° resolution crystal structure of human neuron specific enolase. J Mol Biol 2004; 341:1015-1021.
47. Pancholi V. Multifunctional alpha-enolase: Its role in diseases. Cell Mol Life Sci 2001;58:902-920.
48. Ahmed MU, Thorpe SR, Baynes JW. Identification of N-carboxymethyllysine as a degradation product of fructoselysine in glycated protein. J Biol Chem 1986;261:4889-4894.
49. Watkins NG, Neglia-Fisher CJ, Dyer DG, Thorpe SR, Baynes JW. Effect of phosphate on kinetics and specificity of glycation of protein. J Biol Chem 1987;262:7207-7212.
50. Reed GH, Poyner RR, Larsen TM, Wedekind JE, Rayment I. Structural and mechanistic studies of enolase. Curr Opin Struct Biol 1996;6:736-743.